This invention relates to certain sulfonamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use for controlling undesirable vegetation.
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
U.S. Pat. No. 4,818,275 discloses herbicidal acyclic sulfonamides of the formula ##STR2## wherein, inter alia X and Y are Br, Cl or F;
R is alkyl, haloalkyl or dialkylamino; PA1 R.sup.1 is H, Na, lower alkyl or SO.sub.2 R; PA1 R.sup.2 is alkyl, haloalkyl or lower alkoxy; and PA1 R.sup.3 is halogen, alkyl or haloalkyl. PA1 Y is F, Cl, Br, cyano, nitro, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 haloalkoxy or C(S)NH.sub.2 ; PA1 R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 haloalkoxyalkyl, formyl, C.sub.2 -C.sub.20 alkylcarbonyl, C.sub.4 -C.sub.7 cycloalkylcarbonyl, C.sub.2 -C.sub.6 haloalkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.3 -C.sub.6 alkoxyalkylcarbonyl, C.sub.2 -C.sub.6 haloalkoxycarbonyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl, C.sub.4 -C.sub.7 halocycloalkylaLkyl, S(O).sub.2 R.sup.2, C(O)SR.sup.3, C(O)NR.sup.4 R.sup.5 or benzoyl; PA1 R.sup.2 is C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cylcloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 haloalkoxyalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkoxyalkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 haloalkynyl, C.sub.2 -C.sub.6 cyanoalkyl, C.sub.1 -C.sub.6 nitroalkyl, (CH.sub.2).sub.p --OR.sup.6, C.dbd.CH(CH.sub.2).sub.q --OR.sup.6, C.tbd.C(CH.sub.2).sub.q --OR.sup.6, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.2 -C.sub.6 alkylsulfinylalkyl, C.sub.2 -C.sub.6 alkylsulfonylalkyl, C.sub.3 -C.sub.8 alkloxycarbonylalkyl, C.sub.3 -C.sub.8 alkylcarbonyloxyalkyl or oxiranyl optionally substituted with 1-3 C.sub.1 -C.sub.3 alkyl; PA1 R.sup.3 is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; or R.sup.3 is phenyl optionally substituted with C.sub.1 -C.sub.3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C.sub.1 -C.sub.3 alkoxy or CF.sub.3 ; PA1 R.sup.4 is H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; or R.sup.4 is phenyl optionally substituted with C.sub.1 -C.sub.3 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C.sub.1 -C.sub.3 alkoxy or CF.sub.3 ; PA1 R.sup.5 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; or PA1 R.sup.4 and R.sup.5 are taken together as --CH--CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 0CH.sub.2 CH.sub.2 --; PA1 R.sup.6 is C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.3 haloalkylsulfonyl or P(.dbd.O)(OR.sup.7)(OR.sup.8); or R.sup.6 is phenylsulfonyl optionally substituted with C.sub.1 -C.sub.6 alkyl, 1-3 halogen, 4-5 fluorine, C.sub.1 -C.sub.6 alkoxy, CF.sub.3 or C.sub.2 -C.sub.4 alkylcarbonyl; PA1 R.sup.7 and R.sup.8 are each independently H, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 haloalkyl; PA1 J is ##STR4## wherein the dashed line in J-1, J-5, J-6, J-18, and J-19 indicates that the left-hand ring contains only single bonds or one bond in the ring is a carbon-carbon double bond; PA1 m and n are each independently 0, 1, 2 or 3, provided that m+n is 2 or 3; PA1 Z is CR.sup.9 R.sup.10, O, S, S(O), S(O).sub.2, N(C.sub.1 -C.sub.4 alkyl) or ##STR5## Z.sup.1 is CR.sup.9 R.sup.23, O, S, S(O), S(O).sub.2, N(C.sub.1 -C.sub.4 alkyl) or ##STR6## each R.sup.9 is independently H, C.sub.1 -C.sub.6 alkyl, halogen, hydroxy, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.1 -C.sub.6 haloalkoxy, C.sub.2 -C.sub.6 alkylcarbonyloxy or C.sub.2 -C.sub.6 haloalkylcarbonyloxy; PA1 each R.sup.10 is independently H, C.sub.1 -C.sub.6 alkyl, hydroxy or halogen; or PA1 when R.sup.9 and R.sup.10 are bonded to adjacent carbon atoms they can be taken together with the carbons to which they are attached to form ##STR7## optionally substituted with at least one member selected from 1-2 halogen and 1-2 C.sub.1 -C.sub.3 alkyl; PA1 each R.sup.11 is independently H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 haloalkyl or C.sub.2 -C.sub.6 alkoxyalkyl; PA1 R.sup.12 is H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alklenyl, C.sub.1 -C.sub.6 haloalkyl or C.sub.2 -C.sub.6 alkoxyalkyl; PA1 R.sup.13 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloallyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 haloalkynyl, HC(.dbd.O), C.sub.2 -C.sub.5 alkylcarbonyl or N(R.sup.11).sub.2 ; PA1 R.sup.14 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 haloalkyl or N(CH.sub.3).sub.2 ; PA1 W is N or CR.sup.15 ; PA1 R.sup.15 is H, C.sub.1 -C.sub.6 alkyl or halogen; or R.sup.15 is phenyl optionally substituted with C.sub.1 -C.sub.6 alkyl, 1-3 halogen, 4-5 fluorine, C.sub.1 -C.sub.6 alkoxy or CF.sub.3 ; PA1 R.sup.16 is C.sub.1 -C.sub.6 alkyl, halogen or C.sub.1 -C.sub.6 haloalkyl; PA1 R.sup.17 and R.sup.18 are each independently H, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; PA1 R.sup.19 and R.sup.20 are each independently C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl or C.sub.3 -C.sub.6 haloalkynyl; PA1 R.sup.21 is H, halogen, cyano, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy; PA1 R.sup.22 is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; or R.sup.22 is phenyl optionally substituted with C.sub.1 -C.sub.6 alkyl, 1-3 halogen, 4-5 fluorine, 1-2 nitro, C.sub.1 -C.sub.6 alkoxy or CF.sub.3 ; PA1 R.sup.23 is C.sub.1 -C.sub.3 alkyl, hydroxy or halogen; PA1 R.sup.24 is cyano or C(Q)R.sup.25 ; PA1 R.sup.25 is OR.sup.26 or NR.sup.27 R.sup.28 ; PA1 R.sup.26 is C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 haloalkyl; PA1 each R.sup.27 is independently H or C.sub.1 -C.sub.6 alkyl; PA1 R.sup.28 is H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or NR.sup.27 R.sup.29 ; or PA1 R.sup.27 and R.sup.28 can be taken together as --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 R.sup.29 is H, C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.4 alkylcarbonyl, C.sub.2 -C.sub.4 alkoxycarbonyl or C.sub.1 -C.sub.3 alkylsulfonyl; PA1 Q is independently O or S; PA1 Q.sup.1 is O or S; PA1 p is 1,2 or 3; and PA1 q is 0, 1, 2 or 3; PA1 provided that, PA1 X is F or Cl; PA1 Y is F, Cl or Br; PA1 R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkoxyalkylcarbonyl, C.sub.2 -C.sub.6 alkylcarbonyl, C.sub.2 -C.sub.6 alkoxycarbonyl, S(O).sub.2 R.sup.2 or C(O)NR.sup.4 R.sup.5 ; PA1 R.sup.2 is C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 cylcloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl or C.sub.2 -C.sub.6 haloalkoxyalkyl; PA1 J is J-5, J-6, J-11, J-17 or J-19; PA1 Z is CR.sup.9 R.sup.10, O, S or N(C.sub.1 -C.sub.4 alkyl); PA1 each R.sup.9 is independently H, halogen or C.sub.1 -C.sub.6 haloalkoxy; PA1 each R.sup.10 is independently H, hydroxy or halogen; PA1 each Q is O; PA1 Z.sup.1 is CR.sup.9 R.sup.23, O, S or N(C.sub.1 -C.sub.4 alkyl); and PA1 R.sup.23 is halogen. PA1 Y is F or Cl; PA1 R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.2 -C.sub.6 alkylcarbonyl or C.sub.2 -C.sub.6 alkoxycarbonyl; PA1 R.sup.2 is C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 halocycloalkyl, C.sub.2 -C.sub.6 alkoxyalkyl or C.sub.2 -C.sub.6 haloalkoxyalkyl; PA1 Z is CR.sup.9 R.sup.10 or O; and PA1 Z.sup.1 is CR.sup.9 R.sup.23 or O. PA1 J is J-19; PA1 R.sup.1 is H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylcarbonyl or C.sub.2 -C.sub.6 alkoxycarbonyl; PA1 R.sup.2 is C.sub.1 -C.sub.6 haloalkyl; PA1 R.sup.9 is H; PA1 R.sup.10 is hydroxy or halogen; PA1 Z is CR.sup.9 R.sup.10 ; PA1 n is 1; and PA1 m is 1. PA1 J is J-6; and PA1 Z is CR.sup.9 R.sup.10. PA1 a) (6S-cis)-1-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H- pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide; PA1 b) (6S-cis)-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1 ,2-c]imidazol-2(3H)-yl)phenyl]-N-[(chloromethyl)sulfonyl]acetamide; PA1 c) (6S-cis)-1-chloro-N-[2-chloro-5-(6-chlorotetrahydro-1,3-dioxo-1H-pyrrolo[1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide; PA1 d) (6S-cis)-N-[2-chloro-5-(6-chlorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imid azol-2(3H)-yl)-4-fluorophenyl)-N-[(chloromethyl)sulfonyl]acetamide; PA1 e) (6S-cis)-1-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H- pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monosodium salt; PA1 f) (6S-cis)-1-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H- pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl]methanesulfonamide monopotassium salt; PA1 g) (6S-cis)-1-chloro-N-[2-chloro-5-(6-chlorotetrahydro-1,3-dioxo-1H-pyrrolo[1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monosodium salt; and PA1 h) (6S-cis)-1-chloro-N-[2-chloro-5-(6-chlorotetrahydro-1,3-dioxo-1H-pyrrolo[1 ,2-c]imidazol-2(3H)-yl)-4-fluorophenyl]methanesulfonamide monopotassium salt.
The sulfonamides of the present invention are not disclosed therein.